Hydrogen Peroxide → 6-Hydroxy-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

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Reaction Steps

To a mixture of H2O2 (50% wt in H2O, 0.0115 mL, 0.20 mmol) and CH2Cl2 (2 mL) at −5° C. was added BF3.OEt2. The reaction was stirred at −5° C. for 40 min before a solution of compound 145 (56 mg, 0.14 mmol) in CH2Cl2 (3 mL) was added. The reaction was kept at −5° C. for 10 min and quenched with an aqueous solution of Na2SO3 (2 g, 10 mL). The reaction was diluted with CH2Cl2 and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The CH2Cl2 layers were combined and concentrated in vacuo to give a brown oil. This crude oil was purified by silica gel flash chromatography (eluted with 10% EtOAc/CH2Cl2) to give compound 146 as a yellow solid (32 mg, 64%). HPLC: 90% at 1.89 min (retention time) (Phenom-Prime S5 C18 column, 4.6×30 mm, eluting with 10-90% aqueous methanol over 2 min containing 0.1% TFA, 5 mL/min, monitoring at 220 nm). MS (ES): m/z 357 [M+H]+.

Provenance & Evidence